Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives

Dan Zhu; Yuan Yao; Rong Zhao; Yang Liu; Lei Shi

doi:10.1002/chem.201800555

Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives

Dan Zhu
, Yuan Yao
, Rong Zhao
, Yang Liu
, Lei Shi^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering, Harbin Institute of Technology
Harbin Institute of Technology Shenzhen
Nankai University

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

An unprecedented three-component domino oxidative coupling of diazocompounds for the efficient synthesis of α-azido-β-amino esters with non-activated dimethylamino compounds and simple TMSN₃ was achieved. The main features of this method include metal-free catalysis, satisfactory functional group tolerance, general applicability in complex molecule architectures, and excellent diastereoselectivity in the presence of chiral auxiliaries. In addition, several related control experiments have been conducted to investigate the reaction mechanism.

Original language	English
Pages (from-to)	4805-4809
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	19
DOIs	https://doi.org/10.1002/chem.201800555
State	Published - 3 Apr 2018
Externally published	Yes

Keywords

C−H functionalization
geminal carboazidation
hypervalent iodine reagents
metal-free
three-component coupling

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10.1002/chem.201800555

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title = "Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives",

abstract = "An unprecedented three-component domino oxidative coupling of diazocompounds for the efficient synthesis of α-azido-β-amino esters with non-activated dimethylamino compounds and simple TMSN3 was achieved. The main features of this method include metal-free catalysis, satisfactory functional group tolerance, general applicability in complex molecule architectures, and excellent diastereoselectivity in the presence of chiral auxiliaries. In addition, several related control experiments have been conducted to investigate the reaction mechanism.",

keywords = "C−H functionalization, geminal carboazidation, hypervalent iodine reagents, metal-free, three-component coupling",

author = "Dan Zhu and Yuan Yao and Rong Zhao and Yang Liu and Lei Shi",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = apr,

day = "3",

doi = "10.1002/chem.201800555",

language = "英语",

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journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds

T2 - A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives

AU - Zhu, Dan

AU - Yao, Yuan

AU - Zhao, Rong

AU - Liu, Yang

AU - Shi, Lei

PY - 2018/4/3

Y1 - 2018/4/3

N2 - An unprecedented three-component domino oxidative coupling of diazocompounds for the efficient synthesis of α-azido-β-amino esters with non-activated dimethylamino compounds and simple TMSN3 was achieved. The main features of this method include metal-free catalysis, satisfactory functional group tolerance, general applicability in complex molecule architectures, and excellent diastereoselectivity in the presence of chiral auxiliaries. In addition, several related control experiments have been conducted to investigate the reaction mechanism.

AB - An unprecedented three-component domino oxidative coupling of diazocompounds for the efficient synthesis of α-azido-β-amino esters with non-activated dimethylamino compounds and simple TMSN3 was achieved. The main features of this method include metal-free catalysis, satisfactory functional group tolerance, general applicability in complex molecule architectures, and excellent diastereoselectivity in the presence of chiral auxiliaries. In addition, several related control experiments have been conducted to investigate the reaction mechanism.

KW - C−H functionalization

KW - geminal carboazidation

KW - hypervalent iodine reagents

KW - metal-free

KW - three-component coupling

UR - https://www.scopus.com/pages/publications/85043490940

U2 - 10.1002/chem.201800555

DO - 10.1002/chem.201800555

M3 - 文章

C2 - 29480941

AN - SCOPUS:85043490940

SN - 0947-6539

VL - 24

SP - 4805

EP - 4809

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 19

ER -

Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives

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Keywords

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